In this paper, shakedown of a cohesive-frictional half space subjected to moving surface loads is investigated using Melan’s static shakedown theorem. The material in the half space is modelled as a Mohr–Coulomb medium. The sliding and rolling contact between a roller and the half space is assumed to be plane strain and can be approximated by a trapezoidal as well as a Hertzian load distribution. A closed form solution to the elastic stress field for the trapezoidal contact is derived, and is then used for the shakedown analysis. It is demonstrated that, by relaxing either the equilibrium or the yield constraints (or both) on the residual stress field, the shakedown analysis leads to various bounds for the elastic shakedown limit. The differences among the various shakedown load factors are quantitatively compared, and the influence of both Hertzian and trapezoidal contacts for the half space under moving surface loads is studied. The various bounds and shakedown limits obtained in the paper serve as useful benchmarks for future numerical shakedown analysis, and also provide a valuable reference for the safe design of pavements.